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"Bart is heartbroken when Milhouse and his mother move away to Capital City. Desperate to fill Milhouse’s shoes, Bart attempts to find a new best friend with no such luck. That is, until Marge asks him to wash the family car with Lisa, and the two have so much fun they begin to do everything together as best friends would. Later, Bart decides to pay Milhouse a visit and is shocked to see his once meek best friend has reinvented himself. The new Milhouse sports spiked blond hair, is popular and even gives Bart a wedgie in the halls at school."

During a school field trip, Bart notices a change in Milhouse's behavior. Milhouse talks back to Mrs. Krabappel, wanders away from the group and causes mischief with Bart, and tells Bart he doesn't care what anyone thinks of him anymore. Finally, Milhouse reveals that he is moving to Capital City with his mother.

Bart visits Milhouse in Capital City, only to find that Milhouse has dyed his hair blond, is wearing fashionable clothes, and is cultivating a "bad-boy" image, even going so far as to give Bart a wedgie in front of his new Capital City friends. At home, seeing how depressed Bart is, Marge suggests he spend more time with Lisa. The two begin to bond by washing the car and riding bikes, and after they discover an Indian burial mound together, they become best friends.

Milhouse returns to Springfield when his father wins custody of Milhouse via court order. After she finds out Bart told Milhouse about their secret Indian burial mound, Lisa feels that Bart is acting like their friendship never existed and that he has been using her to fill a void. Bart, however, shows her that he still values her as a sister by giving her a set of cards with nice things he will do for her on them, and the two hug.

At Moe's Tavern, Apu and Manjula are celebrating their anniversary, and Homer realizes he does not have anything for Marge for their anniversary. After being thrown out of the bar, Homer sits on the street and people give him money. He dances and earns enough money to buy Marge some flowers.

Homer continues his panhandling, and eventually makes enough money to buy Marge a pair of diamond earrings. When he continues panhandling afterward, angry bums bring Marge to see what Homer is doing. Marge is mortified and angry, but can not bring herself to throw the earrings away.